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Ordered mesoporous MCM-41 containing cobalt ferrite as high-performance catalyst in the synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides

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Abstract

A multifunctional catalyst with attractive recuperation was manufactured by impregnating 4-dimethylamino pyridine (MP) with Ni supported on MCM-41 coated with CoFe2O4 (MCM-41/CoFe2O4/MP/Ni), which effectively acted as a selective catalyst for the synthesis of tetrazole and selective oxidation of sulfide with high effectiveness. The structures of the hybrid were examined by high-resolution transmission electron microscopies (TEM), field emission scanning electron microscopy (SEM), energy-dispersive X-ray spectrometer (EDS), Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction (XRD), vibrating-sample magnetometer (VSM), elemental mapping, and nitrogen adsorption−desorption isotherm. The hexagonal system of MCM-41 is well preserved after CoFe2O4 and 4-dimethylamino pyridine/Ni embedding. Results showed that the magnetite nanoparticles were coated with the MCM-41 silica with the formation of core–shell structured materials, and the 4-dimethylamino pyridine (MP) was successfully immobilized on the core–shell structured support. In this approach, the MCM-41/CoFe2O4/MP/Ni composite with spherical particles consisted of a mesoporous structure. This catalyst was recovered and reused several times without significantly decreasing efficiency and stability.

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References

  1. N. Moeini, S. Molaei, M. Ghadermazi, Dysprosium (III) supported on CoFe2O4 MNPs as a heterogeneous catalyst for the selective oxidation of sulfides and synthesis of symmetrical disulfides. J. Mol. Struct. 1246, 131071 (2021)

    Article  CAS  Google Scholar 

  2. S. Molaei, N. Moeini, M. Ghadermazi, Synthesis of CoFe2O4@ amino glycol/Gd nanocomposite as a high-efficiency and reusable nanocatalyst for green oxidation of sulfides and synthesis of 5-substituted 1H-tetrazoles. J. Organomet. Chem. 977, 122459 (2022)

    Article  CAS  Google Scholar 

  3. R.Y. Hong, S.Z. Zhang, G.Q. Di, H.Z. Li, Y. Zheng, J. Ding, D.G. Wei, Preparation, characterization and application of Fe3O4/ZnO core/shell magnetic nanoparticles. Mater. Res. Bull. 43, 2457–2468 (2008)

    Article  CAS  Google Scholar 

  4. A. Taguchi, F. Schüth, Ordered mesoporous materials in catalysis. Microporous Mesoporous Mater. 77, 1–45 (2005)

    Article  CAS  Google Scholar 

  5. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli, J.S. Beck, Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature 359, 710–712 (1992)

    Article  CAS  Google Scholar 

  6. M. Ghadermazi, S. Molaei, S. Khorami, Synthesis, characterization and catalytic activity of copper deposited on MCM-41 in the synthesis of 5-substituted 1H-tetrazoles. J. Porous Mater. 30, 949–963 (2023)

    Article  CAS  Google Scholar 

  7. S. Molaei, M. Ghadermazi, Synthesis and characterization of indium and thallium immobilized on isonicotinamide-functionalized mesoporous MCM-41: two novel and highly active heterogeneous catalysts for selective oxidation of sulfides and thiols to their corresponding sulfoxides and disulfides. Appl. Organomet. Chem. 33, e4972 (2019)

    Article  Google Scholar 

  8. S. Molaei, M. Ghadermazi, Selective and efficient oxidation of sulfides and thiols to their corresponding sulfoxides and disulfides catalyzed with praseodymium (III) and dysprosium (III) isonicotinamide (INA) complexes grafted onto modified mesoporous MCM-41. Solid State Sci. 100, 106091 (2020)

    Article  CAS  Google Scholar 

  9. F.R. Benson, The chemistry of the tetrazoles. Chem. Rev. 41, 1–61 (1947)

    Article  CAS  PubMed  Google Scholar 

  10. J. Roh, K. Vávrová, A. Hrabálek, Synthesis and functionalization of 5-substituted tetrazoles. Eur. J. Org. Chem. 2012, 6101–6118 (2012)

    Article  CAS  Google Scholar 

  11. M.A. Malik, M.Y. Wani, S.A. Al-Thabaiti, R.A. Shiekh, Tetrazoles as carboxylic acid isosteres: chemistry and biology. J. Incl. Phenom. Macrocycl. Chem. 78, 15–37 (2014)

    Article  CAS  Google Scholar 

  12. L.V. Myznikov, J. Roh, T.V. Artamonova, A. Hrabalek, G.I. Koldobskii, Tetrazoles: LI. synthesis of 5-substituted tetrazoles under microwave activation. Russ. J. Org. Chem. 43, 765–767 (2007)

    Article  CAS  Google Scholar 

  13. M. Salahuddin, S. Singh, S.M. Shantakumar, Synthesis and antimicrobial activity of some novel benzo thieno pyrimidines. Rasayan J. Chem. 2, 167–173 (2009)

    CAS  Google Scholar 

  14. S. Molaei, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Ordered mesoporous SBA-15 functionalized with yttrium(III) and cerium(III) complexes: towards active heterogeneous catalysts for oxidation of sulfides and preparation of 5-substituted 1H-tetrazoles. Appl. Organomet. Chem. 33, e4649 (2019)

    Article  Google Scholar 

  15. E.A. Popova, R.E. Trifonov, V.A. Ostrovskii, Advances in the synthesis of tetrazoles coordinated to metal ions. ChemInform (2012). https://doi.org/10.1002/chin.201206214

    Article  Google Scholar 

  16. S. Molaei, M. Ghadermazi, Cu attached functionalized mesoporous MCM-41: a novel heterogeneous nanocatalyst for eco-friendly one-step thioether formation reaction and synthesis of 5-substituted 1H-tetrazoles. Res. Chem. Intermed. 47, 4557–4581 (2021)

    Article  CAS  Google Scholar 

  17. N. Fischer, K. Karaghiosoff, T.M. Klapötke, J. Stierstorfer, New energetic materials featuring tetrazoles and nitramines–synthesis, characterization and properties. Z. Anorg. Allg. Chem. (2010). https://doi.org/10.1002/zaac.200900521

    Article  Google Scholar 

  18. Z.X. Chen, H. Xiao, Impact sensitivity and activation energy of pyrolysis for tetrazole compounds. Int. J. Quantum Chem. 79, 350–357 (2000)

    Article  CAS  Google Scholar 

  19. A.M. Khenkin, R. Neumann, Oxygen transfer from sulfoxides: oxidation of alkylarenes catalyzed by a polyoxomolybdate,[PMo12O40] 3. J. Am. Chem. Soc. 124, 4198–4199 (2002)

    Article  CAS  PubMed  Google Scholar 

  20. I. Fernandez, N. Khiar, Recent developments in the synthesis and utilization of chiral sulfoxides. Chem. Rev. 103, 3651–3706 (2003)

    Article  CAS  PubMed  Google Scholar 

  21. A.R. Hajipour, B. Kooshki, A.E. Ruoho, Nitric acid in the presence of supported P2O5 on silica gel: an efficient and novel reagent for oxidation of sulfides to the corresponding sulfoxides. Tetrahedron lett 46, 5503–5506 (2005)

    Article  CAS  Google Scholar 

  22. R. Noyori, M. Aeki, K. Sato, Green oxidation with aqueous hydrogen peroxide. Chem. Commun. (2003). https://doi.org/10.1039/b303160h

    Article  Google Scholar 

  23. S.M. Islam, A.S. Roy, P. Mondal, K. Tuhina, M. Mobarak, J. Mondal, Selective oxidation of sulfides and oxidative bromination of organic substrates catalyzed by polymer anchored Cu (II) complex. Tetrahedron let. 53, 127–131 (2012)

    Article  CAS  Google Scholar 

  24. X.-Y. Hao, Y.-Q. Zhang, J.-W. Wang, W. Zhou, C. Zhang, S. Liu, A novel approach to prepare MCM-41 supported CuO catalyst with high metal loading and dispersion. Micropor. Mesopor. Mat. 88, 38–47 (2006)

    Article  CAS  Google Scholar 

  25. Y. Shu, Y. Shao, X. Wei, X. Wang, Q. Sun, Q. Zhang, L. Li, Synthesis and characterization of Ni-MCM-41 for methyl blue adsorption. Micropor. Mesopor. Mater 214, 88–94 (2015)

    Article  CAS  Google Scholar 

  26. S.K. Roy, D. Dutta, A.K. Talukdar, Highly effective methylated Ti MCM-41 catalyst for cyclohexene oxidation. Mater. Res. Bull. 103, 38–46 (2018)

    Article  CAS  Google Scholar 

  27. N. Moeini, S. Molaei, M. Ghadermazi, Selective oxidation of sulfides and synthesis of 5-substituted 1 H-tetrazoles on Ce (III) immobilized CoFe2O4 as a magnetically separable, highly active, and reusable nanocatalyst. Res. Chem. Intermed. 48, 3109–3128 (2022)

    Article  CAS  Google Scholar 

  28. F. Raji, M. Pakizeh, Study of Hg (II) species removal from aqueous solution using hybrid ZnCl2-MCM-41 adsorbent. Appl. Surf. Sci. 282, 415–424 (2013)

    Article  CAS  Google Scholar 

  29. Z. Zhang, Y. Jiang, M. Chi, Z. Yang, G. Nie, X. Lu, C. Wang, Fabrication of Au nanoparticles supported on CoFe2O4 nanotubes by polyaniline assisted self-assembly strategy and their magnetically recoverable catalytic properties. Appl. Surf. Sci. 363, 578–585 (2016)

    Article  CAS  Google Scholar 

  30. X. Ma, H. Chi, H. Yue, Y. Zhao, Y. Xu, J. Lv, S. Wang, J. Gong, Hydrogenation of dimethyl oxalate to ethylene glycol over mesoporous Cu-MCM-41 catalysts. AIChE J. 59, 2530–2539 (2013)

    Article  CAS  Google Scholar 

  31. A. Elhampour, F. Nemati, Nano-Fe3O4@ TiO2/Cu2O core-shell composite: a convenient magnetic separable catalyst for A3 and KA2 coupling. J. Chin. Chem. Soc. 63, 653–659 (2016)

    Article  CAS  Google Scholar 

  32. M.A. Jani, K. Bahrami, Synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel-curcumin as a robust and extremely efficient green nanocatalyst. Appl. Organomet. Chem. 34, e6014 (2020)

    Article  CAS  Google Scholar 

  33. E. Aali, M. Gholizadeh, N. Noroozi-Shad, 1-Disulfo-[2, 2-bipyridine]-1, 1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1H-tetrazoles. J. Mol. Struct. 1247, 131289 (2022)

    Article  CAS  Google Scholar 

  34. S. Molaei, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Synthesis and characterization of MCM-41@AMPD@Zn as a novel and recoverable mesostructured catalyst for oxidation of sulfur containing compounds and synthesis of 5-substituted tetrazoles. Micropor. Mesopor. Mat 272, 241–250 (2018)

    Article  CAS  Google Scholar 

  35. T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Ni (II)-Adenine complex coated Fe3O4 nanoparticles as high reusable nanocatalyst for the synthesis of polyhydroquinoline derivatives and oxidation reactions. Appl. Organomet. Chem. 32, e3974 (2018)

    Article  Google Scholar 

  36. N. Moeini, T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Anchoring Ni (II) on Fe3O4@tryptophan: a recyclable, green and extremely efficient magnetic nanocatalyst for one-pot synthesis of 5-substituted 1H-tetrazoles and chemoselective oxidation of sulfides and thiols. Appl. Organomet. Chem. 32, e4445 (2018)

    Article  Google Scholar 

  37. A. Ghorbani-Choghamarani, B. Ghasemi, Z. Safari, G. Azadi, Schiff base complex coated Fe3O4 nanoparticles: a highly reusable nanocatalyst for the selective oxidation of sulfides and oxidative coupling of thiols. Catal. Commun. 60, 70–75 (2015)

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are deeply grateful to the University of Kurdistan for the financial support on this research project.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran

    Somayeh Molaei & Mohammad Ghadermazi

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  1. Somayeh Molaei
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Contributions

Mohammad Ghadermazi: Conceptualization, Methodology, Validation, Formal analysis, Resources, Supervision, Project administration, Funding acquisition. Somayeh Molaei: Investigation, Data Curation, Conceptualization, Methodology, Software, Resources, Writing Original Draft, Writing Review and Editing, Visualization.

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Correspondence to Mohammad Ghadermazi.

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Molaei, S., Ghadermazi, M. Ordered mesoporous MCM-41 containing cobalt ferrite as high-performance catalyst in the synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides. J Porous Mater (2024). https://doi.org/10.1007/s10934-024-01594-9

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